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One Year Into the Big Leap

June 18, 2018/

A year ago last week, I officially hung out my shingle for 11th Street Lot Marketing & Publicity, taking a flying leap into the unknown to go into business for myself. I’d reached a breaking point with bad bosses, poorly managed organizations and generally not getting out of my work what I hoped to. So, when I left my most recent festival job in early 2017, I took stock of my options: track down another job working for someone else in the hopes it’d be a fit (both professionally and otherwise), or give it a go on my own.

I am so, so, so glad I chose the latter. So glad. Here’s what I’ve learned in a year of working for myself.

Take the Leap

The hardest part of working for yourself is…you know, the work. You go from contributing to something outside of yourself to something entirely dependent on your own hustle. From a solid paycheck every two weeks to forecasting out income months in advance, saying a silent prayer that the client pays their invoice.

I couldn’t have done five years ago what I’m doing now. I didn’t have the network, the knowledge or the confidence then. I’m not sure I have any of those things now, to be honest, but I have the hustle.

When you come to the edge of all the light you have and must take a step into the darkness of the unknown, one of two things will happen: either there will be something solid for you to stand on, or you will be taught how to fly.

I’m not sure yet if I’ve found solid ground to step out into or if I’m learning to fly, but either way, I’ll never regret having taken that first step into the unknown.

Do What It Takes

It hasn’t always been easy. It certainly hasn’t always been glamorous. While I’ve always managed to pay my rent (and all my bills, actually) each month, there have definitely been some touch-and-go moments, checking my mailbox the minute the postman arrives.

When I started this endeavor, I told myself I’d do whatever I needed to do in order to make it work. Wait tables. Tend bar. Pour coffee. Nanny. Last summer, I was giving walking tours through downtown Chicago. Over the holidays and into the new year, I worked weekends at a shop, the part time income enough to cover my health insurance premium each month.

(That’s right, I have health insurance. File that in the self-employed win column.)

Just last month, I let the shop know that I’d have to depart for good; even a weekly shift was too much. Used to be, I could work on the weekends and take a Tuesday or whatever to run errands and do my laundry. Slowly but surely, that flexibility has narrowed. I realized I needed my weekends back so I could make the most of a full work week.

Just that small step—from working part-time jobs to needing all my time to focus on clients—is a massive milestone!

Send the Email

I don’t think it’s an understatement to say that the majority of my work has been the result of my willingness to ask for it. I can trace most if not all of my clients to emails I’ve sent inquiring about opportunities, suggesting partnerships and seeing what might be possible.

Late last summer, I emailed a friend at the Chicago film festival and ask him to add my name to their list of recommended publicists. I got four clients for that festival, one of which kept me on through April for their theatrical release. Just last week, I sent the same email to the Toronto International Film Festival and a day later, they responded positively that they’d add me to their own list. Any clients I secure as a result would never have happened if I hadn’t mustered the courage to send that email.

And it does take courage! It’s scary to put yourself out there, to open the door to rejection and all but invite it in. But here’s the catch: there’s a chance they’ll say yes. (See above!)

And when the roof over your head depends on it, all of a sudden it becomes a lot easier to send the email.

It’s a Process, and It’s Still Work

I’d like to say this has been the most professionally fulfilling year of my career to date, but that’s not entirely true. I love the work I’ve been able to do, don’t get me wrong.

But some days, it’s much more tempting to just hang out in my PJs until 11a and wait to check my email until my inbox is next to bursting. It’s not like there’s a boss somewhere waiting for me to show up at the office, after all. So yeah, some days I putz around until midday, then get my act together and work like a dog all afternoon.

Of course, some days it’s the other way around. Some days I realize I’ve made wildly unrealistic—if optimistic—promises to clients, so I sit at my computer from sun-up to sundown in order to deliver on those promises. And then, some days an amazing deal for a flight to Madrid hits your inbox and two hours later you’ve blocked off ten days in May to run away from it all.

What I’m trying to say is, I’m still sorting out the best way to go about the actual logistics of working for myself. I’m getting better about routine – wake up, get the day started, sit down to work, break for lunch, work some more, put it all down for the day. More often than not, though, it just doesn’t work like that when your office is also your dining room table. That isn’t inherently bad, but doesn’t make for the ideal work/life balance, either.

Don’t Be Afraid to Say No

A big part of this last year has been learning all kinds of diplomatic but firm ways to say no. No to projects and clients I know I won’t jive with or won’t be able to help. No to opportunities and volunteering that takes me away from the income-producing work I need to focus on. No to the work I can do but know I shouldn’t if I really want to grow.

It’s never easy to turn down a project, particularly when it’s a promising piece and they’re ready to write a check. But sometimes it’s essential. Recently, I was asked to represent a local film premiering at a local film festival. I could’ve easily taken it on, carved out some time this month to reach out to my local network and generate some coverage. But the more I thought about it, the more I recognized that this project, valid as it may be, is not going to serve my business goals in the long run.

If I want this business to grow into what I envision for it, I need to do the work that will get it there. And sometimes, that means turning down work that isn’t in service of that vision.

Stick With It

I’m really proud of this last year; I know it’s no small feat to have kept myself afloat for a whole twelve months, and I don’t want to discount that. But I know I’ve got a long way to go to get to where I want to be. I don’t have it all figured out, but I definitely know a lot more than when I began.

I know I’ll do what it takes to keep myself solvent. I know the work will come, if I’m willing to ask for it (both directly and, you know, of the universe). I know I can say no if I need to. And I know that even if my schedule doesn’t look like every workaday Joe out there, that’s OK. The work is getting done.

Even as I type this, I have a few irons in the fire I’m waiting to hear about. If even one of them comes through, it’ll be exactly the kind of growth I’m aiming for as I head into my second year. It’s scary and exciting and nerve-wracking and exhilarating all at once, and I wouldn’t have it any other way.